Potassium Phosphate, Tribasic → (2-chlorophenyl)-N-{5-[1-ethyl-3-(trifluoromethyl)pyrazol-5-yl](1,3-thiazol-2-yl)}carboxamide

HRID 1524242노트

반응식

HRID 1524242 반응식
Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[O:9])=[N:4][CH:3]=1.[CH2:17]([N:19]1[C:23](B(O)O)=[CH:22][C:21]([C:27]([F:30])([F:29])[F:28])=[N:20]1)[CH3:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC.[Cl-].[Na+].O>CC(N(C)C)=O.O>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]([NH:7][C:5]1[S:6][C:2]([C:23]2[N:19]([CH2:17][CH3:18])[N:20]=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[CH:3][N:4]=1)=[O:9]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 60654727N-(5-bromo-2-thiazolyl)-2-chlorobenzamideHCID 667796632-Ethyl-5-(trifluoromethyl)pyrazole-3-boronic acidHCID 131718255Brine ethyl acetate

생성물 1

HCID 56848140(2-chlorophenyl)-N-{5-[1-ethyl-3-(trifluoromethyl)pyrazol-5-yl](1,3-thiazol-2-yl)}carboxamide수율 14.3%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
150 °C

실험 절차

A mixture of N-(5-bromo(1,3-thiazol-2-yl))(2-chlorophenyl)carboxamide (47, 62 mg, 0.2 mmol), (1-ethyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)boronic acid (58) (62 mg, 0.3 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (1:1) (24 mg) and potassium phosphate (63 mg) in 2 ml DMA and 0.5 ml water was heated under Ar in microwave reactor at 150° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to prep HPLC purification to give 11.5 mg (2-chlorophenyl)-N-{5-[1-ethyl-3-(trifluoromethyl)pyrazol-5-yl](1,3-thiazol-2-yl)}carboxamide (59) as dark brown solid (yield: 14%; purity>90%). LC-MS: calcd. for C16H12ClF3N4OS: 401 (M+1).

후처리

  1. concentrationphase was concentrated
  2. customHPLC purification

출처 및 근거

ORD 기록
ord-3272fcc9785b4ef1bf843a3d4c8d0f04
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079891B2

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